191615-41-5

Basic information

• Product Name: methyl 2(R/S)-amino-3,3-dimethyl-4-pentenoate
• Synonyms: methyl 2(R/S)-amino-3,3-dimethyl-4-pentenoate
• CAS NO: 191615-41-5
• Molecular Weight: 157.213
• Mol File: 191615-41-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 171.4±28.0 °C(Predicted)
• Density: 0.962±0.06 g/cm3(Predicted)
• CAS DataBase Reference: methyl 2(R/S)-amino-3,3-dimethyl-4-pentenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2(R/S)-amino-3,3-dimethyl-4-pentenoate(191615-41-5)
• EPA Substance Registry System: methyl 2(R/S)-amino-3,3-dimethyl-4-pentenoate(191615-41-5)

Safety Data

• Hazardous Substances Data: 191615-41-5(Hazardous Substances Data)

Upstream product

• 192329-91-2 4-(4-fluorophenoxy)benzenesulfonyl chloride 
• 911831-48-6 methyl 2-[(benzyloxy)amino]-3,3-dimethylpent-4-enoate 
• 191615-31-3 3,3-Dimethyl-2-phenylsulfanylamino-pent-4-enoic acid methyl ester 

Relevant articles and documents

Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability

Previous reports from our laboratories described potent tripeptide thrombin inhibitors which incorporate heterocycle-substituted chlorophenyl groups in the P1 position. Using these as lead compounds for further optimization, we identified sites of metabolism and designed analogs with 4-fluoroproline in P2 and cyclopropane-containing side chains in P3 as an approach to reducing metabolism and improving their oral pharmacokinetic performance. The large (300-fold) difference in potency between analogs containing (4R)- and (4S)-4-fluoroproline was rationalized by analyzing inhibitor-enzyme interactions in crystal structures of related compounds and by molecular modeling which indicated that the more potent (4R)-4-fluoroproline isomer stabilizes a proline ring conformation that is preferred for binding to the enzyme. An optimal compound from this work, 41, exhibits high potency in a coagulation assay in human plasma (2×APTT = 190 nM), excellent selectivity versus the digestive enzyme trypsin (Ki = 3300 nM), and excellent oral bioavailability in dogs with moderate clearance (F = 100%, CL = 12 mL/min/kg).

Metalloproteinase inhibitors and intermediates useful for their preparation

PCT No. PCT/US96/19328 Sec. 371 Date Jun. 29, 1998 Sec. 102(e) Date Jun. 29, 1998 PCT Filed Dec. 5, 1996 PCT Pub. No. WO97/20824 PCT Pub. Date Jun. 12, 1997The invention relates to compounds of formula (1) wherein: Z is O or S; V is a divalent radical which together with C* and N forms a ring having six ring atoms, where each of said ring atoms other than C* and N independently is unsubstituted or substituted by a suitable substituent, and at least one of said other ring atoms is a heteroatom selected from O, N and S, and the remainder is carbon atoms; and Ar is an aryl or heteroaryl group; and pharmaceutically acceptable prodrugs, salts and solvates thereof. The invention further relates to pharmaceutically acceptable prodrugs, salts and solvates of these compounds. The invention also relates to methods of inhibiting the activity of metalloproteinases by administering a compound of formula (1) or a prodrug, salt or solvate thereof. The invention further relates to pharmaceutical compositions comprising an effective amount of these compounds, prodrugs, salts, and solvates. The invention still further relates to methods and intermediates useful for preparing these compounds, prodrugs, salts, and solvates.